


Pretty Dee

by NaughtyPastryChef



Category: Supernatural
Genre: Barebacking, Bottom Dean, Claiming Bites, Comeplay, Cross-Posted on Tumblr, Dirty Talk, Feminization, Gift Fic, M/M, Marking, Pictures, Possessive Behavior, Top Sam, cross dressing, excessive use of the word pretty, happy birthday my sweet, nsfw pictures
Language: English
Status: Completed
Published: 2016-09-23
Updated: 2016-09-23
Packaged: 2018-08-16 21:21:21
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,999
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8117986
Author URL: https://archiveofourown.org/users/NaughtyPastryChef/pseuds/NaughtyPastryChef
Summary: Dean has always been pretty in a masculine way but sometimes he just wants to be pretty-pretty.





	

**Author's Note:**

  * For [thep0rnfairy (Jesibella)](https://archiveofourown.org/users/Jesibella/gifts).



> Happy birthday to my sweet, sweet Jes. I hope that you have a lovely day, may it be filled with all the hottest, sweaty, sticky, boys.

Dean has always been a masculine sort of pretty. Even when his face is shaved pre-teen smooth with his legs and underarms to match, he’s still masculine. He’s been too muscular, too compact, to be that willowy kind of pretty perfection.

But none of that means that sometimes he doesn’t try.

He saw them on a website for parody costumes and he fell in love. The color, the cut, the whole outfit. He had to have it. He scrounged up one of his last fake credit cards and dashed into his room to take a few quick measurements before placing the order. The express shipping was already worth it as he felt a thrill rush through his body. He couldn’t keep still; he had to do something now.

“Sammy, heading into town. Need anything from Walgreens?” He yelled into the cavernous bunker, unsurprised when he got a negative grunt in response. “Back later then, call if you need something.” He yelled again as he swung the car keys around his fingers and made his way to the garage.

Long ago Dean ceased being embarassed to buy anything. He liked buying condoms and lube; that way he was always sure to get the right kind. And if some person behind the counter decided to judge his basket of lube and ladies razor blades, scented moisturizer and a few chocolate bars, well, what did he care? They don’t know him; they aren't’ lucky enough to know him.

The three days spent waiting and obsessively checking his PO box are like torture. They have no cases, no plans. They’d agreed on a break at the bunker, just the two of them, trying to get their house in living condition.

“No more accidental curses, Dean. We are cataloguing and locking things away. We have to live here.” Sam cried one afternoon as he sat on the floor and tried to figure out which artifact it was that had switched his feet with his hands.

Finally, the package arrived and it was more perfect than he could even imagine. He forced himself to walk calmly through the bunker and slide the lock on his door quietly so that Sam wouldn’t notice. He’d wanted it to be a surprise.

From long experience he shaved his underarms first, then his legs and then trimmed his pubes, going through the whole pack of disposable razors in the process. He left the small trail of hair from his belly button alone. He took the time to exfoliate his face before shaving as close as he could. He lay a hot towel over his face for the steam and relaxed for a few minutes before moisturizing from the neck down. He trimmed his nails and toe-nails; he’d forgotten the first time he’d bought stockings and they’d been ruined before he even got them on.

Clean and dry and as primped and polished as he was going to be, he stepped back into his bedroom and eyed the outfit on his bed, trying to decide what order to pull the items on in. He started with the panties, then garter. The stockings, carefully lined up and smoothed over his knobbly knees then clipped into the garter. The top he pulled on over his head and then poked his head back around to fix his hair. With a deep breath and a twirl in front of his mirror, he was ready to go looking for Sam.

\---------------------------------------------

Sam was quietly trying to memorize the dizzying array of coded symbols used by the Men of Letters cataloging system when he heard a soft footfall and smelled soft, scented body lotion. A shiver of anticipation ran up his spine before he allowed himself to look up. He gasped; Dean had outdone himself this time.

He looked once for the full effect, then blinked and looked slowly from the bottom up. Black, lacy thigh highs hugged Dean’s legs, leaving a big swath of bare skin at the top, more than enough for Sam to notice, “you shaved for me” and savor the embarrassed twitch of Dean’s thighs. A pink, plaid garter skirt held the stockings in place, highlighting Dean’s skin tone and flat tummy, while making it look like he had curved, feminine hips. His stomach was bare but covering over his pecs and nipples was a matching, pink plaid bra. Flat over the non-existent tits on his brother’s chest but oh-so-enticing still.

Dean’s face was smooth as could be with a light pink flush, from arousal, from embarrassment, who knew. All Sam knew was, “you look so pretty big brother.”

“Thanks.” Dean sighed softly, twisting one stocking covered toe into the floor as he gripped the bottom of the teeny-tiny skirt. “Do-do you wanna see what’s under my skirt?” Dean asked and Sam shot to his feet, his big hands clasping Dean’s hips.

“I do, pretty boy, I really do. But, you know me, I like the suspense. And I think, no I know, that your outfit is missing something.” His fingers tightened and slipped behind Dean to paw at his ass as Dean looked down at himself in shock.

“My marks.” Sam growled into the skin behind Dean’s ear and they both shivered. If Dean’s favorite thing was to play pretty dress up, Sam’s favorite thing was to mark Dean up. To claim him. A different kind of dress up. “Jump on up and wrap those pretty legs around my waist big brother.” Sam smiled, lifting Dean by his ass and already starting his long-legged stride down the hall to their shared bedroom.

Dean nuzzled into Sam’s neck and Sam stumbled, bumping Dean’s back into a wall as he paused to bring their lips together and feel all that soft skin around Dean’s mouth against his stubbled cheek. He finally broke from the kiss to haul Dean more firmly into his arms and continue his way into their bedroom when he tossed his brother onto the bed as though he were a much smaller man.

“I love it when you get all pretty for me Dee. Takes my breath away. Love that you’re still all man under there; big cock just waiting under some pretty panties for me? You gonna let me top this time? Just yank that pretty skirt up and plunge inside? Do I get to get under that pretty matching bra though? Gonna let me up under there and see those little tits?” Sam was breathless with arousal at his own words by the time he was kneeling between Dean’s splayed legs and sliding his hands up the silky stockings.

Sam curled his fingertips under the top elastic of the thigh highs and pulled, letting the elastic slap back down against Dean’s milky, sweet thighs before pressing his lips into the exposed skin. “C'mon big brother, pretty big brother, get those fingers in my hair and pull. Lemme know what you want.” He bit down into the muscle hard enough for Dean to gasp and tear at his hair bringing tears to his eyes.

The pain just made him hornier. He ground his hips into the bed, lamenting that he hadn’t taken off his pants before getting his mouth on Dean. Ignoring the discomfort of his confined cock, he pushed the little skirt up, exposing Dean’s panties and groaned.

They were pink and edged in black lace. They were assless panties. They were barely containing Dean’s thick cock and they were stuff right out of Sam’s fantasies.

 

“Don’t have to waste time pulling them off to the side or anything Sammy. Just, flip me over and go.” Dean hiccoughed, wiggling his whole body around on the bed and lifting his head so that he could meet Sam’s eye.

“Pretty Dee.” Sam crooned, kissing up over the straining of Dean’s cock, then the quivering of his belly, until he got to the bottom of the bralet.

“Gonna let me play with your little nips, big bro?” Sam asked, already teasing his fingertips under the bottom edge of black lace. Dean shivered all over and pressed his chest upwards into Sam’s hands.

“Leave… leave it on though? I wanna…” Dean trailed off, suddenly coming off as unsure about something and Sam paused at his groping to reach up and pull Dean’s face down to meet his own.

“Wanna what?” He asked seriously. There were no secrets between them; not any more. No shame, no embarrassment; only true love and trust. So when Dean cleared his throat and blinked the lust out of his eyes for a moment, Sam knew he’d get an honest answer.

“I wanna see how I look after. Pretty but wrecked by you. I wanna… well, I want you to take pictures of me, after.”

“Oh fuck yes, my pretty boy.” Sam all but growled as he pulled one cup down so that he could suck and bite at Dean’s nipple, while his hand slipped underneath the other cup to pinch and fondle.

Dean was pretty wrecked in no time at all, panties sopping wet with precome, bralet wet with Sam’s saliva, stockings sagging in some places and twisted in others.  Dean rolled onto his stomach and pressed his naked ass into the air. “Need your cock Sammy. Please, I have your marks and now I need your cock.” Dean whined as he waved his hips back and forth.

As he undulated, Sam could see the glint of lube shining from between Dean’s cheeks and he fell forward as he tried to unbutton his pants, smashing his face between those perfect globes and flickering his tongue out to taste his favorite flavored lube on Dean’s skin. His fingers finally fumbled his pants open and shoved them roughly down to his knees, no longer able to wait for anything more. He grabbed his cock and jacked the head a few times, spitting into his palm to ease the way a bit before he pulled back and pressed forward into Dean’s ass.

“Pretty Dee.” He whined as he pressed in, so practiced in the motion and Dean so prepped that he slid inside with one smooth motion.

“Fuck me like you mean it Sammy. Fuck me like you wanna wreck your pretty girl.” Dean panted at him and that was all the encouragement that he needed; his hips were slamming back and forth like a jackhammer, his stomach flexing and contracting with each thrust. His fingers dug into Dean’s sides, leaving crescent shaped marks from his fingernails and bruises that wouldn’t fade for days.

“Ungh yes, Sammysammysammysammy” Dean chanted, the words forced out of his throat with each slam of Sam’s hips to his ass. The bed was bouncing beneath them and Sam could feel the trickle of sweat down the valley of his spine, tickling him. He watched the flowy fabric of Dean’s little skirt bounce back and forth, sometimes hiding and sometimes showing Dean’s excellent taste in panties. He felt the clench of Dean’s whole body and pressed all the way in, grinding his hips instead of thrusting.

“That’s it, make me come big brother.” He leaned forward and purred and that was all it took; Dean was breathless and locked up tight as he came all over himself. The clench of his body milked Sam’s orgasm right out too, Sam forgetting to pull out until his last pulse of come was all he had to decorate Dean’s red, used ass.

On wobbly legs, before he could forget or Dean could change his mind, Sam shoved himself off the bed towards the camera on the shelf in the corner. He was focusing and clicking before Dean had even caught his breath and he had a half-dozen pictures before Dean rolled over onto his back. But he didn’t take back his request; he posed.

He pushed his chest out. He pursed his red, swollen lips. He flipped the skirt up in the front so that Sam could get a picture of his ruined panties.

“Still pretty Dee. So fucking pretty”


End file.
